3,4-dichloro-methylphenidate (3,4-CTMP / 3,4-DCMP)

[Mugz]

Early test data appears to show in-vitro monoamine affinities and ratios somewhere in between MDPV and Desoxypipradrol, but with much relief (given the lack of spare time to spend in the lab) it appears the in-vitro half life is maybe only 4 hours.

Anyone heard anything else about this chem, or have any first hand experience. Would also appreciate comments from the pharmacologists that we have around the site that could comment on whether or not it is theoretically safe.

Wikipedia Entry
PubChem Page

methyl (2R)-2-(3,4-dichlorophenyl)-2-[(2R)-piperidin-2-yl]acetate, 3,4-dichloro-methylphenidate, 3,4-CTMP, 3,4-DCMP, CTMP, DCMP, dichloromethylphenidate

 

[Ceres]

Do you have the IUPAC name or a picture of the structure?

methyl (2R)-2-(3,4-dichlorophenyl)-2-[(2R)-piperidin-2-yl]acetate

Nothing in the literature about this, it's a totally new compound. I wouldn't like to be the first to try it :D

 

[Mailmonkey]

sounds dodge.

Whats your fascination with new compounds that always seem to be a lot shitter than more well known ones (meph)?

monoamine affinities and ratios somewhere in between MDPV and Desoxypipradrol,

somewhere between 2 shit drugs.

 

[Ceres]

it appears the in-vitro half life is maybe only 4 hours.

Horrible use of language. This means nothing.

 

[scottishdnb]

I am looking to approach liquid measurement of this chemical

Any ideas on solubility?

Thanks

 

[Ceres]

If it's in the form of the hydrochloride salt it'll be soluble in water.

 

[scottishdnb]

I believe it is in the form of acetate

in this case, would it be soluble in acetic acid?

 

[babylonboy]

Might be way off base here, but AHA! has a 3,4,-dichlorophenyl ring, perhaps they're knocking this up just because it's convenient synthetically rather than because it's a promising chem?

 

[Ceres]

It would be nice if vendors got into the habit of informing their customers of what salt form the chemical actually is, e.g 3,4-dichloro-methylphenidate hydrochloride. It is actually useful information to have.

in this case, would it be soluble in acetic acid?

What is it you're actually trying to do with it?

 

[Mailmonkey]

he said, for liquid dosing

 

[scottishdnb]

Apparently no NMR, they do believe it is hcl due to melting point of 214 C matching data presented in literature.

info also given: 20mg solubility test in H20 took over 1hr constant stirring.

 

[Ceres]

Quite a world we live in where a vendor can apparently get NMR analysis of their products but they don't even know something as trivial as what acid addition salt form it is.

 

[babylonboy]

What makes you think they don't know what "acid addition salt form" it is?

 

[Ceres]

What makes you think they don't know what "acid addition salt form" it is?

this:

Apparently no NMR, they do believe it is hcl due to melting point of 214 C matching data presented in literature.

info also given: 20mg solubility test in H20 took over 1hr constant stirring.

 

[specialspack]

methyl (2R)-2-(3,4-dichlorophenyl)-2-[(2R)-piperidin-2-yl]acetate

Nothing in the literature about this, it's a totally new compound. I wouldn't like to be the first to try it :D

It's certainly in the literature, wikipedia page gives a number of refs...

 

[Ceres]

So it does, I had searched on reaxys a couple of weeks ago and didn't find anything.. *shrug*

also to babylonboy, the other thing that makes me think vendors don't know what form of salt the stuff they sell is, aside from bullshit product analysis, is the fact I've never seen anything from a uk vendor labelled with that information.

^- and of course, I'm forgetting, the actual admission of more than one vendor that they don't have the slightest clue themselves or reliable independant verification of what it is they are actually selling.

 

[polymath]

The somewhat structurally related 3,4-dichloroamphetamine is a serotonergic neurotoxin... I wouldn't try that RC if I were you.

http://en.wikipedia.org/wiki/3,4-Dichloroamphetamine

 

[Ceres]

From

Synthesis and Pharmacology of Potential Cocaine Antagonists. 2.
Structure-Activity Relationship Studies of Aromatic Ring-Substituted
Methylphenidate Analogs
Howard M. Deutsch, Qing Shi, Ewa Gruszecka-Kowalik, and Margaret M. Schweri

J. Med. Chem. 1996, 39, 1201-1209

Pharmacology. All of the compounds that were
synthesized in this study were tested for their ability
to inhibit the binding of [3H]WIN 35,428 to rat striatal
tissue membrane preparations, as well as the uptake
of [3H]dopamine into rat striatal synaptasomes.[/quote

b. 3- and 4-Position Isomers. The 3- and 4-substituted
compounds with electron-withdrawing substituents
tended to have increased binding potency, whereas
those with electron-releasing groups were little affected
or were less potent than the parent compound. However,
substantial differences exist between the effects
at the 3- and 4-positions. For F, Cl, Br, and CH3 groups,
all of the compounds were more potent than methylphenidate;
3-substitution produced compounds that
were the same or more potent than 4-substitution.
Thus, the most potent compounds tested in this study
are 3-chloro- and 3-bromomethylphenidate (IC50 5.1 and
4.2 nM, respectively). For NH2, OCH3, and OH groups,
substitution in the 4-position did not change potency
greatly, whereas in the 3-position the corresponding
compounds were all less active than methylphenidate
(average decrease by a factor of 3.4). For the larger
nitro and tert-butyl groups, substitution in the 4-position
gave less active compounds. This effect was particularly
large with the tert-butyl compound (1i) which was about
160 times less active than the unsubstituted compound.
Only two 3,4-disubstituted derivatives were synthesized;
the dichloro compound had the same activity as the
3-chloro, while the dimethoxy was 3-fold less active than
the 3-methoxy compound.

...

The somewhat structurally related 3,4-dichloroamphetamine is a serotonergic neurotoxin... I wouldn't try that RC if I were you.

http://en.wikipedia.org/wiki/3,4-Dichloroamphetamine

There's nothing in the papers cited in the 3,4-dichloromethylphenidate wikipedia article that seems to explicitly indicate potential for serotonergic neurotoxicy, but then again they don't appear to actually look for it in the first place...

Unsurprisingly, there is no history of human use of 3,4-dichloromethylphendiate, the papers cited on the wikipedia article only go as far as behavioural studies in rats, self-administration behaviour related to cocaine abuse....

 

[polymath]

^ the molecule obviously contains the dichloroamphetamine backbone, when drawn in that manner

 

[babylonboy]

That skeletal formula is for the R,R isomer, is this what is being sold? I'm surprised if they're selling an enantiopure product, I'd have guessed it would be a mixture of all 4 possible stereoisomers. I think polymath is right, caution is advised here, para-chlorinated phens are not something I'd mess with (unless they were 2,5-dimethoxylated, of course).